Diethanolamides

Description

Diethanolamides
Chemical and physical data

Coconut oil diethanolamine condensate is a mixture of diethanolamides of the fatty acids that constitute coconut oil, which is composed of approximately 48.2% lauric acid (12:0), 18% myristic acid (14:0), 8.5% palmitic acid (16:0), 8% caprylic acid (8:0), 7% capric acid (10:0), 6% oleic acid (18:1, n-9), 2.3% stearic acid (18:0) and 2% linoleic acid (18:2, n-6
Structural and molecular formulae and relative molecular mass

Chemical and physical properties of the pure substance
  • Description: Clear, amber-coloured liquid with a faint coconut odour
  • Boiling-point: 169–275 °C
  • Melting-point: 23–35 °C
  • Density: 0.99 g/cm3 at 20 °C
  • Solubility: Miscible with water at 20 °C; produces an alkali in aqueous solution
  • Octanol/water partition coefficient (P): log P, 3.52
Technical products and impurities
Coconut oil diethanolamine condensate is available in several grades, which differ on the basis of the molar ratio of coconut oil methyl esters and diethanolamine used during their manufacture; the purest product is obtained with a molar ratio of 1:1. Free diethanolamine is present in the final product at concentrations ranging from 4 to 8.5%
In one lot of commercial coconut oil diethanolamine condensate to be used in animal toxicology studies, impurities identified by high-performance liquid chromatography analysis with ultraviolet detection included diethanolamine (18.2%), alkanolamides of unsaturated acids, amine salts of the acids and N-nitrosodiethanolamine
Analysis
Analytical methods to determine the diethanolamide composition of coconut oil diethanolamine condensate have been reported using gas chromatography and high-performance liquid chromatography
Production and use
Production
Coconut oil diethanolamine condensate is produced by a condensation reaction at a 1:1 or 1:2 molar ratio of the appropriate fatty acids (methyl cocoate, coconut oil, whole coconut acids or stripped coconut fatty acids) to diethanolamine at temperatures of up to 170 °C and in the presence of an alkaline catalyst. The 1:2 mixture of fatty acid (or methyl fatty acid) to diethanolamine results in a lower-quality diethanolamide with residues of ethylene glycol and free diethanolamine. The 1:1 mixture produces a higher-quality diethanolamide with much less free amine, which is consequently used at lower concentrations than the 1:2 diethanolamide
It has been estimated that 10 300 and 8650 tonnes of coconut oil diethanolamine condensate were produced in the United States of America in 1977 and 1985, respectively
Information available in 2010 indicated that coconut oil diethanolamine condensate was produced by 10 companies in Mexico, three companies in the USA, two companies each in France and China, Hong Kong Special Administrative Region, and one company each in India and Pakistan. Other sources indicated that it was produced by 15 companies in the USA, four companies in the United Kingdom, three companies each in Germany and Spain, two companies each in Italy and Sweden, and one company each in Belgium, France, and the Netherlands
Use
Fatty acid diethanolamides, including coconut oil diethanolamine condensate, are widely used in cosmetics. In 1985, coconut oil diethanolamine condensate was reported to be present in nearly 600 cosmetic formulations of bath oil, shampoo, conditioner, lipstick and hair dye. The concentration of diethanolamide in these preparations ranged from 1 to 25%. Non-cosmetic applications include use as a surfactant in soap bars, light-duty detergents and dishwashing detergents and as a delinting agent for cottonseed
Coconut oil diethanolamine condensate is used as a corrosion inhibitor in water-based soluble, semi-synthetic and synthetic metal-working fluids and in polishing agents. It is also used widely as an antistatic agent in plastics, e.g. in polyethylene film for food packaging and rigid poly(vinyl) chloride. It has been employed in combination with metallic salts as an antistatic for polystyrene and in impact-resistant rubber polystyrene blends
Natural occurrence
Coconut oil diethanolamide is not known to occur in nature.
Occupational exposure
Occupational exposure to coconut oil diethanolamide in various materials has been inferred from reports of dermatitis, verified by a patch test, among workers; materials identified were barrier creams, hand-washing liquids and metalworking fluids that contained coconut oil, hydraulic mining, and materials used in a printing facility .
 
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Personal care and cleaning products
Exposure to coconut oil acid diethanolamine condensate may occur by skin contact with cosmetic formulations of bath oil, shampoo, conditioner, lipstick, hair dye, soap bars, light-duty detergents and dishwashing detergents
The composition of 2354 registered washing and cleaning agents in the Danish Product Register Data Base in 1992 was reviewed. Of these, 12/70 automotive cleaners, 3/250 detergents for washing textiles, 36/118 dishwashing fluids, 11/94 floor polishes, 83/507 general cleaners, 127/200 shampoos, 9/115 high-pressure cleaning agents and 75/224 skin cleaners contained coconut diethanolamide
1.4. Regulations and guidelines
No occupational exposure limits or recommended guidelines for maximum safe levels in drinking-water have been established for coconut oil diethanolamine condensate.
Exposure data
Coconut oil diethanolamine condensate is a mixture of amides produced by the condensation of coconut oil fatty acids with diethanolamine. Exposure of the general population occurs through dermal contact due to its wide in cosmetics, soaps and detergents. Occupational exposure may occur by inhalation use as a surfactant and skin absorption from some metalworking fluids. Coconut oil diethanolamine condensate may contain diethanolamine as a contaminant.
Other relevant data
The amide linkage between diethanolamine and the fatty acid moiety is resistant to metabolic hydrolysis.
The carcinogenic effects of the coconut oil diethanolamine condensate used in the cancer bioassay may be due to the levels of diethanolamine (18.2%) in the solutions tested. Mechanistic data are very weak to evaluate the carcinogenic potential of coconut oil diethanolamine condensate per se.

Specifications

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